Synergistically active herbicidal mixtures

Abstract

A composition which comprisesa) at least one sulfonylurea of the formula I:wherein the radicals R1 to R5 and the index n are as defined in the specification, or an enviromentally compatible salt of the sulfonylurea, andb) at least one herbicidal compound selected from groups b1 to b41 as defined in the specification, or an environmentally compatible salt of the herbicidal compound,and which exhibits a synergistic herbicidal effect.

We claim:  
     
       1. A herbicidal composition comprising: 
       a) at least one sulfonylurea of the formula I:                    
        wherein:  
       R 1  is C 1 -C 6 -alkyl which carries one to five of the following groups: methoxy, ethoxy, SO 2 CH 3 , cyano, chlorine, fluorine SCH 3 , S(O)CH 3 ; halogen; a group ER 6  where E is O, S or NR 7 ; COOR 8 ; N 2 ; S(O) o R 9 ; SO 2 NR 10 R 11 ; CONR 10 R 11 ;  
       R 2  is hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, C 1 -C 2 -alkylsulfonyl, nitro, cyano or C 1 -C 4 -alkylthio;  
       R 3  is F, CF 3 , CF 2 Cl, CF 2 H, OCF 3 , OCF 2 Cl or, if R 1  is CO 2 CH 3  and R 2  is simultaneously fluorine, R 3  is Cl, or, if R 1  is CH 2 CF 3  or CF 2 CF 3 , R 3  is methyl, or, if R 4  is OCF 3  or OCF 2 Cl, R 3  is OCF 2 H or OCF 2 Br;  
       R 4  is C 1 -C 2 -alkoxy, C 1 -C 2 -alkyl, C 1 -C 2 -alkylthio, C 1 -C 2 -alkylamino, di-C 1 -C 2 -alkylamino, halogen, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy;  
       R 5  is hydrogen, C 1 -C 2 -alkoxy, C 1 -C 4 -alkyl;  
       R 6  is C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 3 -C 6 -cycloalkyl, where these groups may carry 1 to 5 halogen atoms, with the exception of allyl, difluoromethoxy, chlorodifluoromethoxy and 2-cloroethoxy when E is O or S; or in the event that E is O or NR 7 , R 6  is furthermore methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, allylsulfonyl, propargylsulfonyl or dimethylsulfamoyl;  
       R 7  is hydrogen, methyl or ethyl;  
       R 8  is C 1 -C 6 -alkyl, which may carry up to three of the following radicals: halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, C 3 -C 7 -cycloalkyl and/or phenyl; C 5 -C 7 -cycloalkyl which may carry up to three C 1 -C 4 -alkyl groups; C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl;  
       R 9 is C 1 -C 6 -alkyl, which may carry up to three of the following radicals: halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, C 3 C 7 -cycloalkyl and/or phenyl C 5 -C 7 -cycloalkyl which may carry up to three C 1 -C 4 -alkyl groups; C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl;  
       R 10  is hydrogen, C 1 -C 2 -alkoxy, C 1 -C 6 -alkyl, or together with R 11  is a C 4 -C 6 -alkylene, chain in which one methylene group may be replaced by an oxygen atom or a C 1 -C 4 -alkylimino group;  
       R 11  is C 1 -C 4 -alkyl which may carry one to four halogen or C 1 -C 4 -alkoxy radicals; C 3 -C 6 -cycloalkyl;  
       n 0-3;  
       o is 1 or 2;  
       Z is N or CH, or an enviromentally compatible salt of I, and  
       b) at least one herbicidal compound selected from groups b 2 , b 7  to b 9 , b 21 , b 26 , b 27 , b 30 , b 36  and b 37 :  
       b 2 ) amides: allidochlor (CDAA), benzoylprop-ethyl, bromobutide, clorthiamid, dimepiperate, dimethenamid, diphenamid, etobenzanid (benzchlomet), flamprop-methyl, fosamin, isoxaben, monalide, naptalame, propamid (propyzamid and propanil;  
       b 7 ) benozoic acids: cloramben and dicamba;  
       b 8 ) benzothiadiazinones: bentazone;  
       b 9 ) bleachers: clomazone (dimethazone), diflufenican, flurocloridone, flupoxam, fluridone, pyrazolate and sulcotrione (clormesulone);  
       b 21 ) ureas: benzthiazuron, buturon, chlorbromuron, chloroxuron, chlortoluron, cumyluron, bibenzyluron, cycluron, dimefuron, diuron, dymrone, ethidimuron, fenuron, fluormeturon, isoproturon, isouron, karbutilate, linuron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, monuron, siduron, tebuthiuron and trimeturon;  
       b 26 ) phenols: bromoxynil and ioxynil;  
       b 27 ) phenoxyphenoxypropionic esters: clodinafop, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fenoxapro-P-ethyl, fenthiaprop-ethyl, fluazifop-butyl, fluazifop-P-butuyl, haloxyfop-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, isoxapyrifop, propaquizafop, quizalofop-ethyl, quizalofop-P-ethyl and quizalofop-tefuryl;  
       b 30 ) protoporphyrinogen IX oxidase inhibitors: benzofenap, cirnidon-ethyl, flumiclorac-pentyl, flumioxazin, flumipropyn, flupropacil, fluthiacet-methyl, pyrazoxyfen, sulfentrazone and tridiazimin;  
       b 36 ) sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron-methyl, clorimuron-ethyl, clorsulfuron, cinosulfuron, cyclosulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, halosulfuron-methyl, imazosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl thifensulfuron-methyl, triasulfuron, tribenuron-methyl and trifusulfuron-methyl;  
       b 37 ) triazines: ametryn, atrazine, aziprotryn, cyanazine cyprazine, desmetryn, dimethamethryn, dipropetryn, eglinazine-ethyl, hexazinon, procyazine, prometon, prometryn, propazine, secbumeton, simazine, simetryn, terbumeton, terbutryn, terbuthylazine and trietazine;  
       or an enviromentally compatible salt of the herbicidal compound,  
       in a synergistically active amount. 
     
     
       2. The herbicidal composition defined in  claim 1 , comprising a sulfonylurea of the formula I wherein: 
       R 1  is CO 2 CH 3 , CO 2 C 2 H 5 , CO 2 iC 3 H 7 , CF 3 , CF 2 H, CH 2 CF 3 , CF 2 CF 3 , OSO 2 CH 3 , OSO 2 N(CH 3 ) 2 , Cl, NO 2 , SO 2 N(CH 3 ) 2 , SO 2 CH 3 , SO 2 C 2 H 5  and N(CH 3 )SO 2 CH 3 ,  
       R 2  is hydrogen, halogen or methyl,  
       R 3  is CF 2 H, OCF 3 , OCF 2 Cl, CF 3 , or, if R 1  is CO 2 CH 3  and R 2  is simultaneously fluorine, R 3  is Cl, or, if R 1  is CH 2 CF 3  or CF 2 CF 3 , R 3  is methyl,  
       R 4  is OCH 3 , and  
       R 5  is hydrogen.  
     
     
       3. The herbicidal composition defined in  claim 1 , comprising a sulfonylurea of the formula I wherein: 
       R 1  is halogen, a group ER 6 , CO 2 R 8 , SO 2 CH 3  or SO 2 C 2 H 5 ,  
       R 2  is hydrogen,  
       R 3  is F,  
       R 4  is OCF 3 , OCF 2 Cl or OCH 3 , and  
       R 5  is hydrogen.  
     
     
       4. The herbicidal composition defined in  claim 1 , comprising a sulfonylurea of the formula I wherein: 
       R 1  is CF 3 ,  
       R 2  is hydrogen,  
       R 3  is CF 3 ,  
       R 4  is OCH 3 ,  
       R 5  is hydrogen, and  
       Z is N.  
     
     
       5. The herbicidal composition defined in  claim 1 , wherein the herbicidal compound (b) is selected from the group consisting of: 
       bromobutide, dimethenamid, isoxaben, propanil, dicamba, bentazone, clomazone, diflufenican, flurochloridone, sulcotrione, chlortoluron, cycluron, dymrone, isoproturon, methabenzthiazuron, bromoxynil, ioxynil, clodinafop, cyhalofop-butyl, fenoxaprop-ethyl, fenoxaprop-p-ethyl, haloxyfop-p-methyl, cinidon-ethyl, flumiclorac-pentyl, flumipropyn, fluthiacet-methyl, amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfuron, ethoxysulfuron, flazasulfuron, halosulfuron-methyl, imazosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, atrazine, cyanazine, terbutylazine, ammonium-bentazone, cloquintocet, ET-751, F-8426 and KPP-314.  
     
     
       6. The herbicidal composition defined in  claim 1 , wherein the herbicidal compound (b) is selected from the group consisting of: 
       dicamba, bentazone, diflufenican, sulcotrione, bromoxynil, fenoxaprop-ethyl, cinidon-ethyl, amidosulfuron, bensulfuron-methyl, metsulfuron-methyl, nicosulfuron, pyrazosulfuron-ethyl, rimsulfuron, triasulfuron, tribenuron-methyl, atrazine, ammonium-bentazone and cloquintocet.  
     
     
       7. The herbicidal composition defined in  claim 1 , comprising the sulfonylurea (a) and the one or more herbicidal compounds (b) in a weight ratio of 1:0.1 to 1:40. 
     
     
       8. The herbicidal composition defined in  claim 1 , comprising the sulfonylurea (a) and the one or more herbicidal compounds (b) in a weight ratio of 1:0.1 to 1:20. 
     
     
       9. A herbicidal composition comprising 
       a) a herbicidally active amount on a sulfonylurea of the formula I as defined in  claim 1 ,  
       b) a synergistically active amount of at least one of the herbicidal compounds (b) defined in  claim 1 ,  
       at least one liquid or solid carrier and optionally at least one adjuvant. 
     
     
       10. The herbicidal composition defined in  claim 9 , wherein the sulfonylurea (a) and one or more of the herbicidal compounds (b) are present in a weight ratio of 1:0.1 to 1:40. 
     
     
       11. The herbicidal composition defined in  claim 9 , wherein the sulfonylurea (a) and one or more of the herbicidal compounds (b) are present in a weight ratio of 1:0.1 to 1:40. 
     
     
       12. The herbicidal composition defined in  claim 1 , wherein at least one of the herbicidal compounds (b) is a benzoic acid selected from the group consisting of cloramben and dicamba. 
     
     
       13. The herbicidal composition defined in  claim 12 , wherein the weight ratio of the sulfonylurea to the benzoic acid is from 1:0.1 to 1:40. 
     
     
       14. The herbicidal composition defined in  claim 12 , wherein the weight ratio of the sulfonylurea to benzoic acid is from 1:0.2 to 1:20. 
     
     
       15. The herbicidal composition defined in  claim 1 , wherein component b) is at least one compound selected from the groups: 
       b 2 ) amides: dimethenamid;  
       b 7 ) benzoic acids: cloramben and dicamba;  
       b 8 ) benzothiadiazinones: bentazone;  
       b 9 ) bleachers: clomazone (dimethazone), diflufenican and sulcotrione (chlormesulone);  
       b 21 ) ureas: benzthiazuron, buturon, chlorbromuron, chloroxuron, chlortoluron, cumyluron, bibenzyluron, cycluron, dimefuron, diuron, dymrone, ethidimuron, fenuron, fluormeturon, isoproturon, isouron, linuron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, monuron, siduron, tebuthiuron and trimeturon;  
       b 26 ) phenols: bromoxynil and ioxynil;  
       b 27 ) phenoxyphenoxypropionic esters: clodinafop, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenthiaprop-ethyl, fluazifop-butyl, fluazifop-P-butyl, haloxyfop-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, isoxapyrifop, propaquizafop, quizalofop-ethyl, quizalofop-P-ethyl and quizalofop-tefuryl;  
       b 30 ) protoporphyrinogen IX oxidase inhibitors: cinidon-ethyl, flumiclorac-pentyl, flumioxazin, flumipropyn, fluthiacet-methyl, sulfentrazone and thidiazimin;  
       b 36 ) sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, halosulfuron-methyl, imazosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl and triflusulfuron-methyl;  
       b 37 ) triazines: atrazine, aziprotryn, cyanazine, cyprazine, desmetryn, dimethamethryn, dipropetryn, eglinazine-ethyl, procyazine, prometon, prometryn, propazine, secbumeton, simazine, simetryn, terbumeton, terbutryn, terbuthylazine and trietazine.  
     
     
       16. The herbicidal composition defined in  claim 1 , wherein component b) is at least one compound selected from the groups: 
       b 2 ) amides: dimethenamid;  
       b 7 ) benzoic acids: dicamba;  
       b 8 ) benzothiadiazinones: bentazone;  
       b 9 ) bleachers: clomazone (dimethazone), diflufenican and sulcotrione (chlormesulone);  
       b 21 ) ureas: diuron, dymrone, isoproturon, methabenzthiazuron and metoxuron;  
       b 26 ) phenols: bromoxynil and ioxynil;  
       b 27 ) phenoxyphenoxypropionic esters: clodinafop, diclofop-methyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fluazifop-butyl, fluazifop-P-butyl, haloxyfop-methyl and haloxyfop-P-methyl;  
       b 30 ) protoporphyrinogen IX oxidase inhibitors: cinidon-ethyl, flumioxazin, fluthiacet-methyl and sulfentrazone;  
       b 36 ) sulfonylureas: amidosulfuron, chlorsulfuron, flazasulfuron, halosulfuron-methyl, metsulfuron-methyl, nicosulfuron, primisulfuron, prosulfuron, rimsulfuron, sulfometuron-methyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl;  
       b 37 ) triazines: atrazine, cyanazine, simazine and terbuthylazine.  
     
     
       17. The herbicidal composition defined in  claim 1 , wherein component b) is at least one compound selected from the group of: dicamba, bentazone, sulcotrione (chlormesulone), dimethenamid, isoproturon, bromoxynil, fenoxaprop-P-ethyl, clodinafop, cinidon-ethyl, halosulfuron-methyl and atrazine. 
     
     
       18. The herbicidal composition defined in  claim 1 , comprising 
       a) a sulfonylurea of formula (I) wherein R 1  is trifluoromethyl, R 2  is hydrogen, R 3  is trifluoromethyl, R 4  is methoxy, R 5  is hydrogen and Z is nitrogen, and  
       b) at least one compound selected from the group of: dicamba, bentazone, sulcotrione (chlormesulone), dimethenamid, isoproturon, bromoxynil, fenoxaprop-P-ethyl, clodinafop, cinidon-ethyl, halosulfuron-methyl and atrazine.  
     
     
       19. A method of controlling undesirable vegetation, which comprises applying the sulfonylurea (a) defined in  claim 1  and one or more of the herbicidal compounds (b) defined in  claim 1  before, during or after the emergence of undesirable plants, either simultaneously or in succession. 
     
     
       20. A method of controlling undesirable vegetation, which comprises treating the leaves of crop plants and of undesired plants with the sulfonylurea (a) defined in  claim 1  and one or more of the herbicidal compounds (b) defined in  claim 1 , either simultaneously or in succession.